


The Training of Lincoln Loud

by Salacious_Sovereign



Category: The Loud House (Cartoon)
Genre: Age Difference, Feminization, Humiliation, M/M, Older Man/Younger Man, Porn With Plot, Shotacon, Slow Burn
Language: English
Status: In-Progress
Published: 2020-06-14
Updated: 2021-02-04
Packaged: 2021-03-04 00:07:57
Rating: Explicit
Warnings: Underage
Chapters: 6
Words: 9,235
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24714343
Author URL: https://archiveofourown.org/users/Salacious_Sovereign/pseuds/Salacious_Sovereign
Summary: Lincoln Loud, due to an unfortunate accident in the school hallways, now has been forced to be the personal assistant of the school's Principal, Mr. Jones.Little did he know, this decision would begin the path to changing his entire life...
Relationships: Lincoln Loud/Original Character(s)
Comments: 8
Kudos: 24





	1. The Inciting Incident

**Author's Note:**

> Disclaimer: I do not condone any sexual activity with or towards minors. It is a crime almost everywhere worldwide for a reason. Children can not consent, as they have not developed enough nor been taught enough to do so. Keep it fictional.
> 
> Hello there, Salacious Sovereign here! I've decided I'm going to start on something a bit different, because this story will be about Lincoln Loud's path to becoming a subservient sissy slut (alliteration hooo!), so this is your warning now. If that doesn't sound up your alley, just look towards my other stories, where I'll be doing more things with women and girls (mostly girls).
> 
> Also, another thing is that this particular fic is going to be a slow burn style, so we won't be getting to anything really sexy fast.
> 
> With that said, here we go to the start of a new, sexy adventure!

**Notes for the Chapter:**

> Disclaimer: I do not condone any sexual activity with or towards minors. It is a crime almost everywhere worldwide for a reason. Children can not consent, as they have not developed enough nor been taught enough to do so. Keep it fictional.

Lincoln Loud was walking down the hall of Royal Woods Elementary School this morning, looking for all the world like the cat that had caught the canary. His gait was purposeful and sure, his posture radiated delight, and his smile filled his face, giving off to the world that something great had happened recently. Making his way to his locker to deposit his bag Lincoln spotted the camera that had made it's home in his life. "You might be wondering what has me in such a good mood. After all, it's a Monday morning! The bane of school children everywhere!" he said, addressing the camera and gesticulating his point with his hands, "Well a couple things actually. Ms. Johnson told us that this week, we'd be spending our time mixing chemicals and making all sorts of weird things in science class, and that if we did well enough, she'd show us a really cool experiment involving fire! How cool does that sound!

"Of course, it also sounds incredibly dangerous, but I trust that Ms. Johnson wouldn't do this experiment without confidence that everything would be okay, and I trust her, so I have good faith in her decision. That isn't all however," Lincoln continued, rocking in place in excitement of his next statement, "I also finally have enough money saved up for a ticket to Comic Con this year!" He jumped in the hall, pumping his fist in the air to release some of that energy the thought brought him. "I still have to get a costume together however, but that's months away, and I have Leni as a big sister, so I'm not too worried personally."

Lincoln then glanced at a nearby clock in the hall, and said "Well, I've still gotta do school today, so see ya." and continued his walk down the hall. He stopped off at his locker, opening it and placing his backpack on the floor in front of him. He grabbed his things for class and as he shut his locker, he took a quick glance down the hall, and stopped dead in his tracks. There, walking in his direction, was Clara Rutledge.

She was pretty new to the school, having moved from Pennsylvania, and seemed to be a generally nice, girly-girl sort, but not so much so that it was overbearing. She'd been said to have some interests in films, especially foreign ones, as well as tennis. She was nice enough to all the students, though she hadn't gotten particularly close with anyone in particular. Only three weeks since coming here, and she was the most popular girl in school. None of those traits were the biggest contributor to her popularity though, no no no. It was her looks.

Standing at a tall (for her age) 4'11, she had very silky blonde hair, that framed a flawless face of lightly tanned skin. Her green eyes as clear as a freshly polished window and her button nose just begging to be poked. She also has a very rare development for her age; actual boobs! Not the largest to be sure, but for a fifth grader they certainly were noticeable, more so than any other girl at this school. Wearing a light green tank top and pink shorts, she was almost like a Barbie doll come to life, and without question the hottest girl in school.

Clara walked right next to Lincoln, and started opening her locker. The boy in question was having a particularly hard time focusing on anything but the 5th Grade bombshell next to him. After getting her locker open, she noticed Lincoln's attention, and gave a soft "Hello Lincoln, how're you this morning?", all while giving him a smile of pure radiance.

"Oh h-hey Clara!" Lincoln began with a small stutter, "I'm looking forward to our science classes this week actually. Ms. Johnson promising to do a fire experiment sounds really cool."

Clara got a look of delight in her eyes as she said "Oh yeah! I totally forgot about that, just kinda feeling that Monday morning slog, but that sounds like something to look forward to, it could be fun!"

As Lincoln was about to respond, he felt a heavy force slam into his back, causing him to launch forward, and he stretched out his hands on instinct to catch his fall. Unfortunately, this move had his hand latch onto the neck of Clara's tank top, and his hand tangled in it as he fell down, and his weight and speed ripped the front of her tank top clean in half, and with her attempt to back up, leaving her breasts clear open to the whole school.

Lincoln hit the ground with a loud "OOF", and as he tried to reorient himself, all he heard was Clara scream and the sound of footsteps rapidly going away from him, further down the hall. He snapped to attention, and got out a "Clara, I'm so sorry, I-" as he noticed she'd already run off.

He looked on in sadness, that this accident probably cost him his friendship with the new girl, and began to get up, as he heard a throat clearing behind him. Turning, he saw Principal Jones standing behind him, hands crossed and a stern look on his face. "Mr. Loud, I think you should come with me to my office" he said, deep voice resonating through Lincoln's ears as he flinched at the words.

Principal Jones (Lincoln didn't know his first name) was a bit young for the position, at least from his perspective. He only looked like he was around his thirties, but admittedly he could always be much older than that and just take care of himself well. He had a short crew cut, his black hair framed with some slight fades on the side that just had tinges of grey. With a defined, strong jaw, and his slightly rugged face, he was absolutely looking pretty well for himself.

Lincoln knew better than to try and argue with the man, and just followed him as they trudged to his office. They entered the door and passed by the secretary's desk, and he wasn't able to get the best look as he was lightly nudged into Jones' office. Once inside the small room, with just a filing cabinet in the corner, a large desk in the center with two chairs in the front and one large one behind, and a large bookshelf in the opposite corner. Lincoln took a seat across the Principal and sat in silence, waiting for the man to begin.

He needn't wait long, as Principal Jones began with a simple "Lincoln Loud" and a long pause. "You have a pretty good track record at this school Lincoln, at least according to Mrs. Johnson. You try more so than your peers around you, and are routinely reported to be very caring of your fellows. So what changed young man?" he finished, an eyebrow raised in question.

"It was an accident sir, you see I was-" Lincoln started, but the Principal was having none of that. "If that was an accident, it was a pretty harsh one young man. One to expose and humiliate a classmate in front of the whole school, a very pretty classmate at that. Don't think that just because I'm an older man, that I don't know how the mind of a young boy works. That was a pretty deliberate looking attempt to get a peek at Ms. Rutledge's chest, and can be considered a blatant sexual harassment charge, very damaging to both reputation and prospects of life in general."

At these words, Lincoln was left reeling. 'Sexual Harrassment!?' he thought. 'That's awful! I was knocked over by someone in the hallway, there must be camera footage or something!'

The Principal continued on in the silence of Lincoln's internal outrage. "However, there is always the possibility of it actually being an accident, considering your stellar record so far at this school, and because of these factors, I'm willing to give you an alternative option."

At this, Lincoln snapped back to full attention. 'Well, let's hear what the option is, might be easier to get over with than trying to get camera footage.'

Principal Jones then said "Since I know exactly how damaging this can be for you, and with how young you are, i'd rather this not go to full-blown police charges, and just deal with it in-house. I'm willing to have you be my assistant for the remainder of the school year, working under me directly as a detention sort of thing. You'd have to stay after class for an hour or so, and in the morning before class starts. It may seem like a long time, but you must understand how big being labeled as a sexual predator is young man. That's a stigma that will NEVER leave you."

Lincoln was about to retort at that, the school year had just started a month ago, that'd be ages until he was released! But then the last sentence kicked in, and he really thought about it. His sisters would absolutely hate him, and why would they believe his word over the school principal, of all people? Even if he proved himself innocent in the end, a lot of people would be looking at him awfully after that, maybe not those closest, but enough to make a difference.

Lincoln sighed and said "Sir, I truly believe that what happened in the hall was an accident. But, because of the fact that this would hurt not only me, but my family's reputation too, something I can't let happen, I agree. I'll be your assistant for the rest of the year."

Principal Jones nodded his head, saying "Thank you young man, for being reasonable. Also, I'd just like to clarify, even if this was an accident, a female being harrassed so publicly and intensely, by another student no less, puts me in a difficult situation, and I have to give the victim to the benefit of first, in case it wasn't a mistake as you say. I promise, it won't be too harsh, and as a bonus, I'll even put this on your record as community service or a club, so that it can benefit you even more in the long run.

"Heck, now that I'm thinking about it, we could even say that to your family, so that they don't think you're being punished. After all, if we're already punishing you by having you work every day for many months, why have you be punished at home too. Yes, I'll write you a note to take to your parents about your 'decision'.

He then stood from his desk, and offered his hand to Lincoln to shake. The Loud boy didn't feel like it was worthy of a shake, being so negative for him, but the alternative was much worse, so he stood and reciprocated, the too giving a firm shake in agreement.

The Principal wrote down quickly on a post it note from his desk, and handing it to Lincoln, said "Alright then young man, take this note to Mrs. Johnson, and I'll take care of everything else. I'll give you today off, our agreement will start tomorrow morning, so meet me here by 7:00. Good day, young Loud."

Lincoln took the note and fled the room, heading to his class, his mood sufficiently soured. As he slumped through the halls, he faced the ever-present camera and started with "Well, it goes to show that the universe will always equalize itself. Having an amazing day, something has to happen out of my control to ruin it. Welp, I've consigned myself to this, guess I have to see it out.", and with a shrug of his shoulders, went to his class for the day.

Meanwhile, back in the Principal's office, the man in question left his personal room to his personal lobby, mug of coffee in hand, and turned to his secretary, stating "Ms. Wallace, looks like the first step is in place. We've got him secured, now comes the hard part." The woman in question, a redhead in somewhat stimulating office attire, gave a nod of assent and a small smirk of satisfaction, and resumed her paperwork.

His victory claimed, the Principal returned to his office, to begin drafting a lesson plan to make sure that little boy would be under his thumb in body and mind by the end of his work.

It was shaping up to be an eventful year.


	2. An Opportunity for Improvement

**Notes for the Chapter:**

> Disclaimer: I do not condone any sexual activity with or towards minors. It is a crime almost everywhere worldwide for a reason. Children can not consent, as they have not developed enough nor been taught enough to do so. Keep it fictional.

Lincoln Loud is feeling much less excited than he was the previous morning, as he had to report to the Principal's office asap. He trudged through the halls, slouched and dejected, but on his way to where he should be.

Entering the lobby, he once again saw the Principal's secretary, and decided to take a moment to really look at her, since he wasn't being escorted this time. She was beautiful, with red hair put up into a professional bun, a pair of black glasses that gave her an "Office Beauty" sort of feel, and blue eyes that, even looking bored as they stared down at the desk, were attention-grabbing like no other.

He was jolted out of his observation by secretary, Stacy Wallace if her nameplate on the desk was to be believed, addressed him with a "Mr. Loud, I presume?" He gave a nod, and she pointed to the door in the back of the room, saying "Mr. Jones is expecting you, go ahead in." With no other course her walked to the door and opened it, coming into the office where his school year's fate was sealed.

Stepping inside the office, Lincoln saw Mr. Jones sitting behind his large desk, writing on a piece of paper. His head shot up at the creak of the door opening, and a small smile formed on his face as he said "Ah, Mr. Loud. I'm glad you showed up like we agreed, a lot of students would've tried to dodge the responsiblity, regardless of the fact that they'd still be at school for me to find them. Well, I guess that shows the sort of responsibility that enabled me to give you this alternative in the first place.

"Anyways, just put your backpack over there" he pointed towards a corner, where a hat rack stood with a hat and jacket already perched upon it, "and then go to the file cabinet in the corner, 3rd drawer from the top, and just sort the files by date." Giving a nod, he did just that, putting his backpack up and opening the file cabinet.

There actually weren't too many files in there, as Lincoln saw that it was only about a third filled. He shrugged his shoulders, knowing not to look a gift horse in the mouth, and got to his work.

Not even fifteen minutes later, Lincoln had finished the assigned task, and as he closed the drawer, heard the Principal once again address him with a "That fast? Hmm, well I guess there wasn't too much in there then. Well Mr. Loud, why don't you take a seat in front of me, let's talk a bit more about our arrangement."

When he saw the boy was seated, Mr. Jones continued. "I figure that, since you're done with your work and we'll be together for quite some time, we should get to know each other, at least a little."

"Well okay then" said Lincoln, "What do you wanna know Principal Jones?"

"Well one thing that's interesting about you, and you must really get a lot, is the fact that you have ten siblings, all sisters too. How is it living in that house?"

"Well sir" Lincoln started, a bit relieved to begin on a topic that's safe, "it's pretty hectic, with that many people under one roof. There are of course, the ups and downs. On one hand, privacy is almost impossible with so many people running around, and it's really hard to get some quiet. Guess we really live up to that last name." Jones gave a soft chuckle, and motioned with his hand for Lincoln to continue. "On the upside though, you've got a lot of people to go to if you want help with something, and you're never really alone when it comes to dealing with problems. It's nice, knowing that so many sisters have my back."

He frowns suddenly. "Though, sometimes those ten are on the other side. When you make someone mad, they tend to ALL get mad..."

Jones' eyebrow raises as he hears this. "Oh really? Being the subject of ten people's ire, some of them older than you too, must be pretty difficult to deal with."

Lincoln gives a sigh "Yeah, that part isn't really fun, but it happens pretty often, sadly." He gets a far off look, and in a weary tone, says "It's just- when that happens, I can't help but feel kinda helpless, there's really nothing I can do to change their mind or stop them from doing whatever they want at that point. Heck, even the sisters that are normally pretty calm and cool, like Luna or Leni, just join in, never asking my side or if it's deserved. It's just the downside of being a boy with ten girls I guess."

"Well," the Principal starts, "what if it didn't have to be?"

Lincoln snaps to attention at those words. "What do you mean by that? Uh, I mean sir." Lincoln quickly corrects himself.

Jones gives a small chuckle. "Don't worry Mr. Loud, you don't have to be so formal with me. Just Garret will do, it's my first name after all. Or Mr. Jones, whatever works for you young man. Actually, would it be okay if I started referring to you as just Lincoln?"

Lincoln gives a nod, "Sure, that's fine. But what-" The Principal holds up a hand, stopping him in his tracks.

"Yes I know, the mob thing. Well, Lincoln" he says with an emphasis, "what I mean is, you don't have to be the sole boy among girls, at least from their perspective. 

"See, if you can understand them, maybe not as your sisters, but as girls, then you might have an easier time dealing with them, and even derailing those sorts of ten versus one situations before they can even begin."

Lincoln scratches his head at this. "Princip- I mean, Mr. Jones, I can kind of see your point, but how would you know any of that? No offense sir, but you're clearly a man from what I can see, how would you get how girls work?"

Mr. Jones reaches to a corner of his desk, and turns a picture frame towards Lincoln, showing a photo of Mr. Jones, a lady that looks around his age, and three girls of varying heights and ages. "I'm a father of three girls, and I had to learn how a woman works when I married one. I'm pretty educated on the matter."

Lincoln makes an 'O' shape with his mouth as the information hits him. "That makes sense, yeah." He taps his chin a bit, thinking.

The Principal sees this, and says "Perhaps I can say two words that might sway your opinion?" Lincoln looks at him, clearly curious. "Girl Guru." he says with a flat stare, and the boy can do nothing but scratch the back of his head and blush, looking away towards a far corner of the room as he recalls the tragic fate of his and Clyde's business project.

"Heheh, yeah that's a, REALLY good point..." He shakes his head to clear his thoughts, and looks at Mr. Jones, and in a resigned tone says "Well, okay then Garret, we can do that for sure."

He feels a hand on his shoulder and looks up to see the Principal kneeling at his side, a soft expression on his face. "Lincoln, it's my job as the Principal of this school to help my students. If that means with their school life or their home life, then that's what I'll do. So, after school today, come to my office, and we'll do something about your sibling troubles, okay?"

Lincoln nods his head enthusiastically, a big smile breaking out as he feels the compassion in Mr. Jones' words. As he's about to open his mouth, he hears the bell ring, shocking him out of his movement.

"Well Lincoln," the Principal says as he takes a notepad and starts writing on it, holding it out to the boy after a moment "You better get to class. And remember, after school okay?"

Lincoln nods his head and grabs the offered paper, goes to grab his backpack, and rushes out the door, at least as much as he can do without running. "Thanks Mr. Jones, see you later then!" he says on his way out.

Lincoln Loud may have not started this day in the brightest of moods, but it seems like it's gonna work out after all.


	3. Talking to Girls

**Notes for the Chapter:**

> Disclaimer: I do not condone any sexual activity with or towards minors. It is a crime almost everywhere worldwide for a reason. Children can not consent, as they have not developed enough nor been taught enough to do so. Keep it fictional.

RIIIIIIING!

A loud bell was heard throughout Royal Woods Elementary, and the children all celebrated, some loud and openly, others quiet and internally, as their day of education comes to a close, and they can look forward to their lives outside of school for the remainder of this Tuesday. But one student is not going home, no, he's staying behind to go meet with the Principal, one Lincoln Loud.

The white-haired boy in question packed up his backpack with less fervor than he normally would due to this fact. But he was not sad, no in fact, he had looked forward to this meeting all day, craving the answer to his largest dilemma with his sisters; the complete imbalance of power due to numbers. The issue had plagued him for as long as he could remember, and now the start of a solution was in his sight! All he had to do was go meet up with his Principal, one Mr. Garret Jones, and listen to his experience and advice. So, with a subdued but still present air of excitement about him, the boy finished packing his bag, and headed down the hall to the Principal's office. 

As he strolled down, he idly wondered what advice he would be offered. Maybe trying to get in touch with his feminine side? But how, he was already a decently feminine boy, what with liking Dream Boat, his knowledge of beauty pageants, and skill with sewing. "Well," he decided, "I'll see when I get there".

The boy was suddenly shaken out of his reverie by a call to his name, and he looked for the source of his voice, and stopped dead in his tracks. There, just a bit down the hall, was the beautiful Clara Rutledge, waving at him and calling down "Lincoln Loud!" with a small smile on her face. He snapped out of his shock, and quickened his pace to go meet with the 5th grade beauty.

As he got closer to the girl, she began to speak to him, saying "Hey Lincoln, how're you doing?" with a polite yet cheery tone. Lincoln swallowed, trying to calm his nerves, as he responded with a shaky "F-Fine Clara. What'd you call me over for?" At that, the girl's small smile turned into a frown, and she looked to the side, scratching her arm lightly in nervousness. "I wanted to apologize Lincoln, since that guy yesterday caused you to be in trouble for something you didn't do. I heard from the other kids in the hall what the Principal said, and I just had to at least let you know I don't hold anything against you, I was there after all, and everything was a complete accident."

Lincoln calmed down at this heartfelt expression of regret, and was quick to respond with a hurried "No no, it's fine. Yes I am getting punished, but I managed to make a deal with Mr. Jones that'll be super helpful for me, so I guess it all worked out in the end. Also, I mean, I still ripped your shirt in the hallway, that probably wasn't fun."

At his words, Clara visibly relaxed. "Oh that's so good to know that you're making the best of it. But don't worry, as I said, ACCIDENT." she enunciated the syllables clearly, attempting to get her point across. "And I can always get a new shirt, it's not a big deal. Still, even if your punishment isn't as bad as you thought, I would like to make it up to you, so would you like to get some ice cream this weekend? I know this super nice cart in a park across town, and I feel that would be a good start to let you really know how sorry I am."

Lincoln's cheeks darkened at her words. 'ICE CREAM?! ON A WEEKEND?! THAT'S BASICALLY A DATE!" he screamed internally, and took a moment to force himself to calm down, and play it cool so as to not lose this golden opportunity. "S-sure thing Clara" he stuttered, "that'd be pretty fun, how about we meet in the other park, y’know, Royal Woods Park, as I don't really know the one you're talking about."

Clara beamed at his words, an expression that made the boy's heart melt. "Oh, okay Lincoln! Well, I have to go catch my bus now, but I'll see you around, AND on Saturday! Bye!" she called as she waved at him again, moving past and making her way to the school's entrance.

"Bye Clara!" Lincoln yelled after her, waving energetically with a goofy smile plastered on his face. 'Oh MAN' he thought, 'a weekend outing with Clara. This punishment is really shaping up to be a good thing after all.' He stood there, looking forward to the weekend, when his thoughts reminded him of something. "Oh right, I still gotta go to Mr. Jones for my lesson." he said to himself, and moseyed down to the man's office, in a great mood to begin his lessons.

He walked in the door as normal and Ms. Wallace let him know that Mr. Jones was a bit busy at the moment, and so he settled into one of the chairs to wait. He wasn't sitting for very long when he heard Ms. Wallace say "You know," and looked at her, to see the secretary's gaze focused entirely on him, causing the boy to squirm a little in his seat as the attractive lady studied him. After a long pause, she continued. "Garret is a very nice man, really willing to help the unfortunate or just people who don't know any better. Hell, he even helped me once, a long time ago when I was still a teenager."

Lincoln put aside his nervousness to focus entirely on the woman's words, now intrigued. "I came from a bit of a bad home, don't want to get into those details right now, but let's say I had to leave to solve those issues. But that only brought up new issues, as I was now a fifteen-year old homeless girl, out on the streets, no home, no food, and no friends willing to help.

"I ended up beginning to beg at some busy intersections, but wasn't really raking in much money, only enough to really eat every other day, sometimes not even that. I was beginning to get desperate, the hunger and just sadness I was feeling driving me more and more to sink even lower in order to live." At the boy's confused face, Stacy Wallace sighed and blurted out "Prostitution, kid. I was thinking about having sex for money." and Lincoln's eyes widened and his cheeks reddened at the thought, half aroused as he imagined the woman in front of him naked, half shocked that she'd be willing to do such a thing. Then again, it sounded like a rough time...

"But then one day, a car pulled up to my stop, and I was set to ask for change as normal, when the window rolls down and there's Garrett, giving me the most thoughtful look I'd ever seen. He looked me over, and told me to get in the car. Now normally, I would've denied him for sure, but he had such a look of sympathy when he said that, and his voice was so soft that I obeyed without thinking.

"Once I was in the passenger seat, he drove off and began talking, telling me that he'd seen me around here for a while now, and wanted to ask what had led to here. So, I told him my tale of my home and my decisions that lead to here, and what I was thinking of doing next. He told me that there was an alternative, that he was in need of a secretary, and had a spare bedroom in his house that I could stay in until I felt I was ready to move one.

"I broke down crying, this was the first bit of real compassion I'd felt in months, as the other homeless people were all perverts who just wanted my body, and most regular people would barely give me the time of day. In tears, I thanked him a whole bunch, and asked him why he'd want to help me, as I was just a dirty homeless girl he didn't know. He didn't respond for a second, and when he did he just asked me how old I was. I responded without hesitation, and he smiled at me, a sad smile, and simply said: "No one that young should have to suffer." So you see Mr. Loud," she said, drawing Lincoln back into the real world, "Mr. Jones is a great man, and while the circumstances that got you into his office weren't the best, the man will help you out where you need it." and with that, she returned to her work, typing away at the computer on her desk.

Lincoln used the silence to think about what he heard, that helping people seemed to just be part of Mr. Jones' nature, and that he was really in a better situation for it. He was interrupted by a loud buzz coming from Ms. Wallace's desk, and she said "Well, looks like you can go meet with that great man now." as she waved towards the door.

Lincoln got up from his seat, stood right in front of the door, and looked at the frosted glass. 'Garret Jones - Principal' it said. 'And Great Man' Lincoln amended in his mind, a soft and warm smile on his face as he put his hand on the doorknob.


	4. Starting the Lessons!

**Notes for the Chapter:**

> Disclaimer: I do not condone any sexual activity with or towards minors. It is a crime almost everywhere worldwide for a reason. Children can not consent, as they have not developed enough nor been taught enough to do so. Keep it fictional.

As he opened the door to the office, Lincoln saw Mr. Jones at his usual spot, filling out some form on his desk. His head however, looked up as he heard the squeak of the hinge, and upon seeing the boy's face, a small smile graced his features. "Lincoln, my boy! Come in, and we'll start on that lesson just as soon as I've finished this paper." And Lincoln did so, hanging up his backpack before sitting down in the increasingly-familiar spot in front of the large desk.

After a half-minute of some scribbling, Mr. Jones dabbed the paper dramatically and exclaimed "There!" as he swiped his pen away with a flourish and put the paper into a small pile to his left. He then turned to Lincoln and started speaking. "Well Lincoln, to start with, how's your day been going so far?"

The boy thought for a moment, and with a smile said "It's been fine sir, I've actually been looking forward to coming here all day! It's just nice to have a start to solving one of the biggest problems me and my sisters have, y'know?"

Mr. Jones smiles widely. "That's great then Lincoln, I'm very glad to have you eager to learn! Well, to begin Lincoln, let's begin with women in general. Obviously you've learned from your failed venture that girls are varied and different, but what generalities, if any, can you think of right now?"

The Loud boy put his hand on his chin, thinking about it for a while, before tentatively responding "... Well, I know all of my sisters, as different as they are, all are obsessed with chocolate. From the genius to the jock, they sure do love those candies. Um, what else..." he trailed off, looking to the ceiling and ruminating further.

"Oh!" he snapped his fingers suddenly, "They all love romance! They can't help but get involved literally every time there's a girl involved, whether we're just friends or not, and they all love the show Dreamboat and watch it religiously. Though I can't say anything about that last one, I do it too." he finished sheepishly.

"Well," starts Mr. Jones, hands clasped together on his desk, "that's a good starting ground, but as we've established, women tend to have different personal interests, and while it's good to learn them, it honestly just might not be feasible, depending on how many you plan to befriend. After all, there's only so much time in a day. So the answer would be getting a deeper understanding of all women, so that you have a much firmer knowledge and experience base to draw from. Obviously, you're a bit too young to have that sort of experience, ten sisters or no, so what do you think would be an effective way to get to know ALL women at once. Maybe not personally, but generally?"

"I know that to get to know someone, you have to spend time with them, but you said there's not enough time in the day, and with my sisters I totally get that. But I can't really think of a way to get to know all girls at once Mr. Jones."

"Have you ever heard of the phrase 'Walk a mile in their shoes' Lincoln?" At the boy's head shake, he went on. "It means that to really get to know someone, you'd have to understand how they live. Live a portion of their life. Obviously, that's not entirely possible, as we are who we are, not who they are, but what we can do is simulate the experience.

"As an example, what's the most obvious difference between men and women as a whole? Don't answer that, it's a rhetorical question" he quickly said before Lincoln could utter a word. "It's clothing my boy. Or at the very least, clothing is the very tip of differences between men and women. Think on the types of clothes your sisters wear, would you be liable to wear any of those outside of specific circumstances?"

Lincoln gave it some thought. He definitely wouldn't want to wear the dresses of his more feminine sisters, like Lola and Leni. He wasn't sure about the long socks some favored, like Lucy and Luan. Lori usually wore really short-shorts and open shirts, and that might be a bit too revealing for him. Luna and Luan also wore skirts too. Really the only one's he could see himself wearing would be Lana and Lisa's, but he's not sure when or why he'd wear overalls, and the backwards cap was a no. And Lisa probably wore her clothes because it covered a lot for chemical splashes or something, not because of fashion reasons. So yes, he could see Mr. Jones' point.

"Alright, I see your point." said Lincoln, projecting his thoughts soundly for the Principal, "but what does that have to do with me?"

"I'm glad you asked. You see Lincoln, one thing I've come to see about women and their clothes is that the two are inseparable. Even the more boyish women have a much preferred outfit. Mind you, so do men, we like to look and dress nice, but there's not much variety to us. It's either pants or shorts, short-sleeves or long-sleeves, maybe a jacket. That's a bit of an exaggeration, but do you get what I'm saying?"

He did, and nodded so, and the Principal continued. "Women however, have oodles of different outfits to choose from. They have dresses, both long and short, thin and thick. For shirts, they have long, short, and no sleeves, they have camisoles and tank tops and blouses and even tunics!

"They have pants and shorts like us, but they also have skirts, different types of pants like flared ends or skinny jeans. They have sport shorts and denim shorts. And that's not even to get into colors! They wear all colors of the rainbow, from reds and blues, to greens and yellows. Tell me young man, when was the last time you've seen a man or boy wear either pink or purple?"

Lincoln couldn't remember any, so he shook his head negative. "Exactly. So, with this large variety of outfits, it makes a certain amount of sense that females would all enjoy trying to mix and match to at least some degree. And that's what we're going to be focusing on.

"You, Lincoln, tend to wear the orange polo and blue jeans, a very nice but casual men's attire. I'm going to ask two things of you today. And the first is this: I want you to attempt to wear something different, but not something strictly male."

"Uhm, Mr. Jones sir" Lincoln began, a bit of nervousness creeping into his voice, "are you sure that'd be okay? I mean, wouldn't the other guys in school start making fun of me and stuff? Not to mention it'd just be really embarrassing..."

The Principal gave off a small chuckle. "Oh Lincoln, I know, but what I meant by something not strictly male is clothes that could be worn by either gender. Are there any clothes you could see your or your sisters wearing, and no one would care either way?"

Seeing his point, Lincoln gave a slow nod, and Jones continued. "So, I'm saying to wear some clothes of that sort. Some white shorts, or a dark green or light blue short. Nothing that screams female clothes or anything, just something to begin to get the idea of what women's clothing is like. Trust me, I had to do even more extreme for my daughters when they were young. Have any of your sisters forced you to wear a glittering tiara, or a pink apron with red hearts?"

At the boy's face, Mr. Jones let out a hearty laugh. "That's exactly what I felt then. But don't worry," he said, calming down from the humor of the moment, "I'm not asking anything that extreme. Tell me, since you have ten sisters, the baby notwithstanding, are there any you could ask for advice on what would be acceptable to wear?"

"Leni." Lincoln answered without hesitation, having been thinking of this since he was clarified, "She would give me good advice, and is also nice enough to not make fun of me or anything for it. I'd just have to make sure she can keep it quiet from the others."

"Well then young man, there's your first piece of homework, if you will. I know that word sparks unequaled dread in children, but let's just call it what it is, hmm? Wear something more gender neutral tomorrow, and get your sister to help then, if you feel she would without misunderstanding or being rude about it.

"Remember, Lincoln. This is to help you understand your sisters, and solve the ganging issue, okay? I don't do this as a prank, or a practical joke. I do this to help your home life. So go, catch the bus or walk home, whatever you need, and let's start that path to work out your problem. Goodbye, Lincoln, I'll get your progress tomorrow."

A bit unsure, but with a set goal in mind, Lincoln gave a tentative goodbye, and walked out of the office, thinking on how to ask Leni without the other girls getting wind of it.


	5. Fashion on the Mind

Lincoln stepped out of the front doors to his elementary school, deep in thought about how to go about Mr. Jones' assignment for him. He really didn't want his sister to misconstrue him, and while that didn't seem too likely with Leni, he also knew the chance of her telling other accidentally was nowhere near zero, and he definitely wasn't sure what they'd all think. He'd have to keep this quiet somehow, do his darndest to not let at least his more malicious siblings know.

Lori was busy doing something, so he and his younger siblings would be walking home. He stood on the steps for a while, waiting for the others to show up, and eventually they did. Lisa, Lola, Lana, Lucy, and his older sister Lynn all showed up within the next few minutes, and he went with them to home.

The walk seemed to be pretty standard, as much as he could see not paying attention anyway, when he felt a hand on his shoulder and turned to see Lucy in her usual morose way gazing at him. He could never truly tell where she was looking due to her bangs, but it was a safe bet that she was looking at him all things considered.

"What's up Lucy?" he asked, doing his best to remain casual and hide his thoughts. She nudged her head over her shoulder and began to slow down, and he took the hint and fell back from the group to afford themselves some privacy.

"You seem stressed, brother. What issue plagues you so?

"What do you mean Lucy, I'm perfectly fine!" Lincoln proclaimed, a nervous energy painting his voice.

Lucy's face got even more impassive if that were even possible, and pointed down at him. "Your hands are shaking."

He looked down and sure enough they were, just enough to be noticeable. He put some effort into steadying them and they calmed down significantly.

"Okay so maybe I'm not feeling the best" he admitted, a blush adorning his cheeks, "but this isn't really something I can just talk to anyone about. Well, I can kind of, but as weird as it might seem, I actually plan to talk to Leni about this."

That got the girl surprised, at least as much as could be seen with Lucy's hair covering most of her face. "That's pretty strange, yes. But, if you already plan to talk to one of our sisters about it, then I guess it's no issue." She then grabbed placed her hand on Lincoln's shoulder. "But if you should find that your misery cannot be fixed so easily, definitely visit me dear brother. My coffin lid is always open for family."

Lincoln felt touched, even with how strange that sounded to him, and he gave his younger sister a pat on her hand before they resumed their walk home in a comfortable silence. 

* * *

Most of his day home had been spent pretty normally. He did his homework, solved a small dispute between the twins, and reread one of his favorite Ace Savvy comics. But even with the relative lack of stress, Lincoln was pretty anxious about today. He'd asked Leni earlier if he could talk to her in private after dinner, and that was finished a couple of minutes ago.

He was currently pacing in his room, waiting for his sister to come in. Just the idea of this conversation was getting him really anxious, but he had to go through with this. After all, he was the one who asked for lessons, and he'd learned long ago about assuming he knew it all. That 'Girl Guru' feels like it'll haunt him forever...A knock at the door interrupts his internal reverie, and he quickly psychs himself up enough to face this day, and opens the door. He sees the kind, wide smile of Leni staring down at him.

"Hi Lincoln!" she says very loudly, waving excitedly at him. He's split between groaning at her volume and enthusiasm, or smiling at her kind nature. He opts for the latter as he says "Hey Leni, come on inside" and steps around to let her in. He closes the door behind her, and she swiftly takes a seat on his bed.

"Gosh, your bed is so soft Linky, it's like, totes nice!" she exclaims as she rubs her hand all over his sheets. "Yeah I know Leni, you say that every time you come in here." he says good-naturedly, knowing that the nicer he is, the easier this conversation will be.

Speaking of which, he should really get started on that. "Well Leni, I called you in here to ask a question. Specifically, one about fashion." He cringed as the loud squeal erupted from her mouth, and he quickly moved to quiet her with his hand. "But I don't want anyone else to know, so just _please_ stay quiet about this!"

She nods her head and speaks, but it's muffled by his hand, and he moves it away. "Don't worry little Linky, I'll keep it safe and sound! So, what'd you wanna know?" she says.

"Well, I have a bit of a personal... let's call it a project, and for it to work, I have to change my wardrobe a bit. Specifically, I have to try wearing some clothes that either a girl or a boy could be comfortable with. Can you help me?"

She puts a hand on her chin and looks at him confusedly. "But like, aren't you already comfortable in your clothes? And jeans aren't like, the most comfy thing ever, but they should be comfy enough or you'd wear something else right?" She then gasps, slapping her hands on her cheeks, her eyes going wide in shock. "Unless you've been super UN-comfy for years because of your pants! Oh I'm so sorry I didn't see sooner, we'll totes get you some super soft pants!" She stands up suddenly, a look of determination in her eyes.

Lincoln waves his hands at her. "No, Leni, not like that, I'm fine with my clothes. What I meant was, something that I could wear that's not either a boy's or girl's outfit, one that you could see either one wearing and not think, 'That's a girl's outfit' or 'Those or boy's clothes', y'know?"

He sees the understanding replace the previous determination in his sister's eyes. "Oooh, I see, you want something androgynous!" At his incredulous stare, Leni puts her hands on her hips and glares at him. "I know some big words Lincoln, especially when you need them to describe clothes."

She relaxes her posture and continues. "Don't worry though Lincoln, I bet we can find you something super adorbs to wear for sure, and won't make you look either way!"

Lincoln mentally sighs in relief, as this really hadn't gone too bad. However, he feels he spoke too soon as he feels Leni's iron grip on his wrist. "Come on, we'll go get you a makeover!"

As Lincoln is dragged off to what will no doubt take up the rest of his evening, he feels some measure of acceptance. ' _Well_ ', he thinks, ' _at least I won't look stupid._ '


	6. Inklings of Style

" -and I think an aquamarine tee would go **great** with these pants I have here..."

Lincoln and Leni had went into the latter's room at her insistence to find a perfect outfit for Lincoln, and the two were feeling very different about the challenge. Leni, of course, found the whole endeavor to be super fun, as she really didn't get the opportunity to decide on men's fashion very often, and with the man in question being her little brother, she definitely wanted to do her very best by him!

And as she rambled on to herself about colors and clothing combinations that would look the best, her brother sat on her bed (Lori would probably kill him for being on her bed, Leni's permission or not) feeling rather nervous. He wasn't one to change up his outfit too often, as he'd already found a style that he liked and that suited him. Changing that up seemed rather... jarring for the young boy, as it'd be such a drastic change to a well-established routine. But he quashed down his fears with a reminder that this was for the better in the long run, that with Mr. Jones' guidance he'd be one step closer to solving his biggest issue with his siblings.

But he was brought out of his internal reverie by a loud call of "I've got it!" He focused on his sister turning around, arms outstretched and displaying two pieces of clothing for him. In her left hand was a polo not unlike what he'd previously worn, except the color was a weird one. It was a halfway point between orange and pink, though it definitely looked more on the pink side, and that did nothing to comfort the male Loud.

The other was a pair of shorts, white but not so much so that they would reflect light like it was a flashlight. He was definitely okay with this piece of the outfit, but looking at the shirt, he couldn't feel anything but nervousness inside...

"I've found something that will be great for you to wear Linky! This salmon polo is a classic men's piece, and the white shorts will go with, like, _anything_ , so it'll work out perfectly! Why don't you try it on now?" Leni said, shaking the clothes at him, an excited smile lighting up her face.

But Lincoln couldn't face the idea of wearing something so close to pink, he had to stand his ground! "Leni, look, I trust you with fashion way more than I'd trust myself. But that shirt's _pink_. You can call it salmon all you want, it's pink, and I asked you for clothes I could wear and not look like a girl!"

Leni put her hands on her hips, tutting as she shook her head. "Lincoln, salmon is not pink, they're totally two different colors. And besides, it's a classic color for men's fashion! So just try on the clothes please!" She pouted at him, giving Lincoln the biggest and softest eyes he'd seen her muster.

Lincoln looked at her pleading expression and nearly relented to his sister's request, but his eyes drifted over to the shirt, and his resolve strengthened once more. "No, Leni, it's just... too close to pink for me to wear, I'll be made fun of for sure. Please, can you just pick something else?"

His sister opened her mouth to retort, a somber expression on her face, before she was interrupted by the bedroom door opening. The two siblings turned their heads simultaneously to see the eldest Loud child, Lori, enter through the room. Her eyes were intently focused on her phone's screen, and her fingers were a blur of motion, texting faster than most could type on a keyboard. She idly shut the door behind her, but as she took a step into the room she froze in her motions. Her head slowly turned away from her phone to stare at her younger siblings in front of her. She took a moment to stare at them, assessing the scene before speaking in a confused tone.

"Leni, what is Lincoln doing in here?"

Leni turned towards her only older sister, an annoyed expression marring her features. "Lincoln wanted me to get him some nice clothes, but he won't wear the ones I picked out for him!" She thrust the shirt in front of her. "He keeps saying that this shirt is pink! Look Lori, tell him it's _clearly_ not pink, and he'd look super adorbs wearing it!"

Lori looked the shirt over for only a moment before turning to her brother and giving him a flat stare. "Lincoln, that shirt's not pink. It's obviously salmon, and men wear salmon shirts all the time."

"See! That's what I said!"

Lincoln sighed. "Look Lori, I get that it's got a different name, but you just can't look at that shirt and say it's not pink! If not for you, for the other kids at my school! They'd make fun of me for sure if I wore that!"

Lori, sensing this would be a bit more of an argument than she wanted to deal with right now, quickly tapped her screen in a flurry of fingers. "Look Lincoln, I'm being dead serious when I say men, _very manly men_ , wear salmon." Before her brother could say a word, she turned her phone's screen towards him. "Look for yourself if you don't believe me."

Lincoln closed his mouth and stared at the screen. The words _Salmon men's shirt_ were at the top, and all throughout were pictures of very handsome men, better looking than the ones on _Dreamboat_ even, wearing outfits very similar to the ones Leni had in her hands. Some were obviously models in a studio, but there were others of men on the streets wearing shirts of that color, and they looked confident and perfectly fine wearing such... girly looking colors. Sure, some weren't salmon and white shorts, or even had salmon as the shorts rather than the shirt, but they all looked very nice and perfectly fine with the clothes they were wearing. No one was mocking them, no one looked the slightest bit apprehensive, and they all looked good in the clothes too.

Knowing that he'd lost the argument by a long shot, his head drooped down and he exhaled. "Okay you win, those guys _do_ look good in those clothes. Fine, I'll wear them Leni." he said, outstretching an arm for his sister to deposit the clothes in.

Leni squealed in excitement and thrust the clothing into his hands. "I promise Linky, you'll look amazing in these!"

Lori gave a slight smirk as she saw her brother studying the clothes in his hand. "Exactly. And besides," she said, pulling up and showing Lincoln another picture on her screen. "Salmon and orange are so close of colors that it's just almost like you're wearing the same shirt anyways."

Lincoln shifted his attention away from the clothes he now held, and studied the screen in front of him. Sure enough, a circle filled with the two colors was displayed to him, and he saw that really, they were _incredibly_ close together. Honestly side-by-side, they looked so close it was kind of hard for the boy to tell them apart. His shoulders relaxed as some of the tension left him. "Yeah, I guess you're right Lori. Thanks you two, I'll go try these on now." And with that, he got up, gave his sisters a hug each, and walked out of their room, intent to go try on his clothes.

Leni looked to Lori, a small sincere smile on her face. "Thank Lori, I know Linky's gonna like totes cute in that, he just has to know to wear them that's all!" She then walked out the door as well, following her brother down the hall so she could judge her decision in person.

Lori stood there alone in the room, phone in hand, mentally patting herself on the back for helping out one of her siblings so smoothly. She made to go get dressed into something more comfortable to wear around the house, before realization struck her.

'Why would Lincoln be looking for new clothes to wear?'


End file.
